My First Time(s)

I have liked women's clothes since I was young. I had a large dresser and a chest of drawers in my room. That was way more storage space than a young boy needed so my mother stored a lot of her older clothes in there. It was the time when I was "coming of age" and I used to lock the door and try on her things.
When I was 18-19 I had a girlfriend who liked to swap underwear.That was my first taste of wearing panties. It really turned her on to see me wearing her small, tight underthings.She was a very thin girl and her panties were pretty uncomfortable to wear. When she got tired of me stretching out hers she started buying me my own. She also began to slip a finger or two inside of me during blowjobs. She knew that it would make me cum hard and quickly. As all good things do , it ended. She moved away but I got to keep the panties!
By this time my compounded experience of trying on the clothes, wearing panties and really enjoying the feel of her fingers inside of me made me really curious about what sex with a guy would feel like. I soon got my chance.
I was at a party where I knew very few people. I am and have always been pretty quiet and shy. I do open up a little after a few drinks. A guy sat down next to me and began talking. He seemed like a pretty nice guy albiet a little full of himself.I was kind of a rocker back in the day. I had fairly long hair, always wore concert tee's and jeans. He began commenting on my pretty hair and telling me how cute I was. I blushed and said thanks but I felt uncomfortable. Being the shy type I am, I excused myself to go the bathroom and get another beer.
A little later he found me again. This time we'd both had more to drink and he was much more forward. "You have the cutest little ass that I've ever seen and I REALLY want to put my dick in it."
"I..I..don't know. I've never done that before." was my reply.
"You will love it" he promised, slurring his words.
" I'm not really attracted to guys," I slurred my words,"but i would like to know what it feels like."
"Come on, I just live down the street". So I went.
Things moved rapidly when we got there.Right to the point I guess. He started removing his clothes as soon as the door closed.
It was big....very big.. to this day probably the biggest I've ever seen personally. He was already rock hard.
They say hindsight is 20/20. If I hadn't been drunk maybe I would have told him that there was no way that giant thing was going into my tight virgin( a couple of slender girl fingers don't count) rear end, but I didn't...
It hurt. It hurt a lot.I protested but he told me it only hurts at first. It hurt the whole time. Luckily he came very quickly.
I laid there for a few minutes with his cum sprayed all over my back wondering if my ass was broken. He had disappeared into the bathroom. I could hear him throwing up. When he came out he just said" Thanks, now get dressed and go."

Well, now I knew what it felt like and I was never going to do that again...but that was a lie.

About a year later I went to a cookout with some co-workers. There was a guy there that hadn't been working with us long. He was a skinny long-haired geeky guy who shared my interests in music and comic books. When they ran short on chairs he offered to run back to his place to get some. He asked me to come along to help.
On the way there he started into what I thought was a peculiar line of questioning. He was very nervous. Questions like "Did I like girls?", "Do I dress to be comfortable?, "What kinda things turn me on?
As we arrived at his place I finally asked him" what gives, why the questions?"
Turns out he had caught just the briefest glimpse of my shiny pink panties I guess maybe I bent over or something. I explained that I wasn't really attracted to guys that I just wore them to turn me on.
I could tell by the snugness of his shorts that he was excited. Something overcame me and I asked him if he would like to see?
I dropped my shorts to model for him based on my previous experience that was as far as I intended to go. He began to rub his erection through his shorts. I told him it was okay and soon he had his cock out stroking it. It was rather small, smaller even than mine...so I thought "What the hell", pulled my panties down and invited him to enter me.
Keep in mind I am very shy and this was way outta character for me but this guy was just so sweet and innocent. I'm not sure he'd ever even been with anyone before. He was kind and gentle and lasted a lot longer than Mr. Horsecock did. He came on my ass and I just pulled up my panties and wore his cum for the rest of the day. We never did anything like that again and a month or so later he took another job and moved away.

I decided that sex with guys just wasn't really my thing. As much as I did like that 2nd time It just didn't feel right. Something was missing. That was many,many years ago.
Then Carrie Anne appeared...